Cottage vacation rentals in Orange County

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Orange County

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Locust Grove

5.0 out of 5 average rating, 106 reviews

Quaint & Cozy LakeView Cottage - Lake of the Woods

Welcome to Brent and Carla's Lake View Cottage! Our beautifully renovated, fully furnished, unique and luxurious home is stocked with everything you need to enjoy your stay in beautiful Lake of the Woods. Our cozy cottage is a perfect get-away for your next vacation, visit with family, work trip, staycation or weekend getaway. You will instantly be set at ease as you enter our home featuring wonderful décor, detailed craftsmanship and lots of amenities to make your stay relaxing and memorable.

Nov 28 – Dec 5

G$49,093 GYD per night

Guest favorite

Cottage in Orange

4.91 out of 5 average rating, 130 reviews

Willie's Place Country Cottage Pets Allowed

Step out your front door and pet horses located next door. Willie's place is newly renovated and has all the amenities you need. Located close to wineries, shopping, wedding venues, Historic Montpelier, Corn Maze, Town of Orange, Woodberry Forest School, 10 minutes to Gordonsville, 30 minutes to Charlottesville. Kayak the Rapidan, take a horseback ride at Oakland Heights or see a play at Barboursville. Exposed beams throughout, a beautiful Loft and back porch for sitting. You won't go wrong.

Sep 25 – Oct 2

G$37,748 GYD per night

Guest favorite

Cottage in Orange

4.95 out of 5 average rating, 365 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

Oct 16 – 23

G$22,645 GYD per night

Guest favorite

Cottage in Gordonsville

5.0 out of 5 average rating, 127 reviews

Merry View Cottage

Our newly renovated farm cottage sits at the edge of a grove of giant hardwoods. Enjoy year round mountain views, including Merry Mountain. Ease into the morning while watching wildlife from a front porch rocker. Visit local wineries, breweries, restaurants, museums, shops, hiking trails or wedding venues. Unwind in the hammock or practice yoga on the back deck. Prepare dinner in our full size kitchen. Then, star gaze around the fire-pit after dark. This peaceful oasis awaits you.

Dec 16 – 23

G$32,068 GYD per night

Guest favorite

Cottage in Ruckersville

4.92 out of 5 average rating, 96 reviews

Historic Estate: The Cottage Near Charlottesville

One of the great Southern sporting Estates has been a 5* destination for the past five years for overnight stays, weddings, and events. We would be delighted to welcome you to The Cottage, The Carriage House, or The Pool House. (Listed separately) Located on a 550-acre estate with 9+ miles of woodland trails with spectacular views of the Blue Ridge Mountains. Work or relax playing on our two tournament pickleball courts, saltwater pool, or swim in our natural spring-fed lake.

Jan 6 – 13

G$49,078 GYD per night

Superhost

Cottage in Madison

4.92 out of 5 average rating, 147 reviews

Charming Guest Cottage at Winery

Early Mountain Vineyards' charming Guest Cottage, nestled next to our front block of grapevines and below our historic hilltop barn, offers breath-taking views of the Blue Ridge Mountains and a serene place to watch the sunset while sipping wine. Only short distance to our Tasting Room - open 5 days a week, Thursday - Monday. We recommend a reservation in advance - this can be made via our website, Early Mountain Vineyards, or by calling our winery directly.

Jun 10 – 17

G$63,740 GYD per night

Guest favorite

Cottage in Rochelle

4.9 out of 5 average rating, 20 reviews

Location, Location 29 & 231 with a 5 star clean

Mile of Sky Cottage is nestled off the road and sits on almost 4 acres of land. The property boasts a large front yard perfect for playing a game of football, or some stargazing at night - just wait until you see that night sky! Prefer a little shade? Step out back where you can set up a game of cornhole, or build a fire in the inground fire pit. There is a small 2 level deck, where you'll find a propane grill and additional seating.

Jun 24 – Jul 1

G$41,195 GYD per night

Superhost

Cottage in Gordonsville

4.88 out of 5 average rating, 8 reviews

Charming Cottage Stay at Spotswood Lodge

Located on an 11-acre farm in the midst of Central Virginia’s wine country, the Cottage at Spotswood Lodge is a sanctuary for all who visit. The Cottage’s rustic charm speaks to its bygone days as the caretaker’s home for the original farmhouse, now known as Spotswood Lodge. Enjoy exclusive private access to this beautiful property by renting the Cottage (sleeps up to 7 guests and is equipped with a kitchenette - fridge/microwave only).

Jul 14 – 21

G$96,072 GYD per night

Guest favorite

Cottage in Spotsylvania Courthouse

4.88 out of 5 average rating, 120 reviews

Bond House: Historic Retreat at Walnut Grove

Escape from the city to a historic 1740s cottage with a distant view of the Blue Ridge Mountains and peaceful surroundings with the opportunity to experience the slower pace of country living. Spend the day at Lake Anna to swim/ kayak/ boat or visit the state park, just 5 minutes away. Enjoy local wineries, and explore historic Civil War battlefields. After a fun filled day, return to your private oasis with a fully equipped kitchen.

Sep 7 – 14

G$24,963 GYD per night

Guest favorite

Cottage in Ruckersville

4.91 out of 5 average rating, 267 reviews

Lake Haven Cottage

Make yourself at home at our peaceful 1-bedroom cottage that has everything you need for your trip to the Blue Ridge Mountains. The cottage comes with heating, AC, Washer+Dryer and DIRECTV. During your stay, you can also enjoy using a convenient private bathroom, kitchen, and living room. Our Airbnb is within driving distance to UVA, the Skyline Drive & Shenandoah National Park, local wineries, craft breweries and much more!

Dec 29 – Jan 5

G$21,527 GYD per night

Guest favorite

Cottage in Gordonsville

5.0 out of 5 average rating, 52 reviews

Shade Tree Cottage: Pet Friendly + Fire Pit

Are you looking for a relaxing getaway weekend in Virginia's countryside? Welcome to the Shade Tree Cottage! This home dates back to the Civil War and is full of cottage vibes. Located just a 3-minute drive from downtown Gordonsville, the home is the perfect combination of rural retreat and launching point to some of Central Virginia's best wineries, historic sites, and area attractions.

Jun 14 – 21

G$43,558 GYD per night

Guest favorite

Cottage in Madison

4.96 out of 5 average rating, 332 reviews

THE PERFECT HIKING & WINERY COUNTRY RETREAT

Welcome! Our charming 2 bedroom guesthouse is located in the middle of our 23 acre farm. Currently the property is being used for livestock - cattle (and one donkey named Jasper). Please note: The pool will be open the first week in May thru Labor Day Weekend (sometimes longer if weather permits).

Sep 27 – Oct 4

G$25,293 GYD per night